The Winds of Your Career

I’m a road cyclist. It’s one of my favorite hobbies, and since I’m about to embark on a week long ride in the greater Yellowstone area, I might as well pay some tribute to the sport here – and share an awkward bike selfie with you (this is me with my friend Beth – also a cyclist and a friend I made by stalking her in the locker room when she was my spin instructor…but that’s another story).

When you’re a road cyclist, you get pretty familiar with wind. Headwinds. Tailwinds. Crosswinds. There is rarely an outdoor ride when wind doesn’t play a contributing factor. It’s just a fact of riding.

I got to thinking about how these winds play a role in your career after watching the amazing HBO documentary series, The Defiant Ones (if you haven’t watched it yet and like music at all – go watch it now!). Jimmy Iovine (who I admittedly had never heard of before the series) talks about how he started using fear as his tailwind and that became the real shift for his career.

I glommed onto it because of my cycling experience and my quest for all things related to career success and satisfaction. While I’m pretty sure he never talked about fear as a headwind, as a cyclist, I know that the headwind is the obvious corollary to the tailwind. And the more I thought about it, the more I realized how relevant this concept of wind in your career is for so many people.

The Headwind of Your Career

Unless you’ve done some reflective work about your career, my guess is you understand the concept of a career headwind. The career headwind slows you down, makes everything feel like a battle (regardless of progress), and generally wears you out.

If you’re like most people, I’m willing to bet that fear is your headwind. It’s something you have to overcome, charge through, and “just get over.” Fear becomes an obstacle to moving forward as it slows your progress – or at least makes it more painful.

How does fear hit you in the face and slow your progress in your career?

  • It stops you from trying something new.
  • It prevents you from taking initiative for fear of being wrong.
  • It limits your thinking to keep you confined in a nice, tidy (albeit lonely and dark) little box that makes sense to others.

When you’re hindered by fear, you know that to move ahead you have to make your mark, but you’re so afraid of making the wrong mark, that instead you do nothing. You stay comfortable, you show no initiative, and you let that fearful wind hit you smack in the face and keep you from progressing.

Fear as a headwind is exhausting. It’s what allows people to stay in a role that is “good enough” even if it’s not what they want to be doing.

Sometimes it’s slight and you can’t figure out why you’re losing steam and going slower than normal when you’re working just as hard.

But the drain is real no matter the speed, and just like in cycling, a headwind always catches up with you.

What About the Crosswind?

When you’re on the road on a bike, you also encounter the dreaded crosswind. To me, crosswinds are way worse than headwinds. A crosswind comes at you from the side and it’s not as obvious why you’re worn out and going slower than normal, but it hits you nonetheless and it’s all you can do to stay upright and keep moving forward.

A crosswind in your career is hopefully rare. A career crosswind feels like nothing is going right. You’re battered and can’t keep yourself straight and just feel beat up. It’s not that you’re fighting anything head on – you’re just worn out.

I have a client now who’s in the middle of a three year career crosswind. He’s at a startup company, and while his performance is great with no complaints, he just can’t seem to get his bearings under him. He feels like he’s being pummeled and not able to use his talents appropriately.

After working through the first phase of Strategy Sessions with me, it’s become so clear why he can’t stay up right in his career! He’s in a fast-paced, “ready – fire – aim” culture, and his strengths and preferences lie in a more deliberative pace. So, while he wants to really sink into business data and create some long term, sustainable plans for his business, the culture of his company is precisely the opposite.

The kicker is that now he knows it and can propose a role in his company that is more suited to who he is and hopefully transition that crosswind into a tailwind (see below)!

Crosswinds are confusing. They’re not totally in your face, but you feel out of sorts and a little battered day in and day out.

It’s like you’re constantly trying to right your course (or your bike), but can’t seem to get into the groove. Like my client, some awareness and a little action can shift your wind into…

The Coveted Tailwind

You know those people that seem to have so much energy, a smile on their face, and get more effective work done than everyone else? Don’t they suck…a little?

The truth is – they have an advantage. They have a career tailwind.

As a cyclist, I love a good tailwind. You never really notice a tailwind. You just think you’re killing it and going way faster than normal (all this training is paying off!) without much effort. It’s great.

A career tailwind is often described as drive and it feels a lot like a tailwind on the bike. People experiencing it have a mission and a purpose. Those who have chosen a calling as their work often exude this idea of a tailwind. Those who focus on the impact of their work generally have a tailwind, too.

The good news is you can shift your current career RIGHT NOW to get that tailwind feeling. All it takes is a little self- assessment and understanding what you really want out of your career to make a turn and right your course.

If you’re not sure how to start, check out the Strategy Spotlight. It will highlight why you don’t have that tailwind-I-can-do-anything attitude and give you concrete next steps to shift your winds.

What about you?

What kind of wind are you facing in your career? Share below if any of this rings true for you and you’re looking for a shift.


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